Whitney Wolfe, the founder and CEO of Bumble, has made matchmaking her business. Her dating app is 20-million-users strong and well known for its feminist approach to the online courting process—when two heterosexual users are matched, a connection can only be made if the woman makes the first move. (The company has since expanded its reach with the launch of Bumble BFF in March of 2016 and Bumble Bizz earlier this week.)

As fate would have it, for the entrepreneur and her now husband, Michael Herd (who’s a restaurateur as well as in the oil-and-gas business) sparks first flew IRL as opposed to virtually, but their love story still started with Whitney unabashedly taking the lead.

It was just before Christmas in 2013, and the two were on vacation in Aspen with their respective families when a mutual friend introduced them one afternoon. The next day, that same friend and Whitney came barreling down the slopes only to find Michael having a long, leisurely lunch on what was a very optimal ski day. “I sat down next to him and was giving him a hard time about wasting such amazing conditions,” remembers Whitney. “Michael admitted he didn’t know how to ski, and being from Utah and having grown up skiing, I was perplexed as to why someone who couldn’t ski would be on a ski vacation.” He quickly suggested she teach him how.

“I was up for the challenge and excited to slyly show off my skills,” Whitney says. “So up the gondola we went. I spent every minute of that long ride boasting about my expertise. He said that he was nervous and suggested that I go slow so he could keep up. When we got off, he picked up my skis and got me clicked in. I thought, Hmm, that’s weird, that’s kind of a pro move, but then quickly started down the hill. I went as fast as I could and thought he was long behind me. Next thing I know, he passes me backward. When we got to the bottom, he clicked off my skis, handed them over, and said, ‘Y’all have a good day!’ My life has never been the same since!”

After leaving Colorado, the two spent hours on the phone, but didn’t see each other again until the end of January. They started dating officially on Valentine’s Day, and a proposal came in June two years later.

“In typical Michael fashion, I had no idea it was coming,” Whitney admits. “He told me two things that morning: 1) He wasn’t sure marriage was in the near future as we were both so young and busy with our careers, and 2) We were going to his family’s ranch that weekend.” Michael’s usual truck was in the shop, so they needed to take a much older one, which meant no air-conditioning for a four-hour drive in the Texas heat. They made two fast-food stops on the trek: “Lots of greasy french fries made for super-cute proposal skin!” says Whitney with a laugh. “I also hadn’t put on a stitch of makeup and could not have been more casual if I tried after that haul.”

When they arrived at the ranch, Michael insisted they go on a trail ride despite the fact that Whitney was a novice horseback rider. “He said he was going to take a quick shower, but insisted I didn’t need to. As a result, he looked amazing and fresh in a white button-down and jeans. Me on the other hand? Well, he tossed me an XL men’s fishing shirt and told me to button it to the top for bugs, and that super-casual look I had going on was taken to a whole new level!”

Once wardrobe changes had been made, the two set out on the ride. After an hour, Michael suggested they stretch their legs and take in the sunset. They hopped off their horses, and he got down on one knee. “Turns out he had the ring in his pocket the whole time,” says Whitney. “It was just the two of us, in the most special place to us in the world, no one around for miles. It was absolutely magic! We cried and laughed the whole way down the hill.”

A few days after they got engaged, Whitney and Michael took off on a trip to Italy. It was a vacation that had been a long time in the making, but Whitney never imagined they’d be celebrating their engagement. “He had festivities all lined up,” remembers Whitney. “From the day after we got engaged, I went into full wedding mode—as one does—and he started making a funny Chewbacca ‘bridezilla’ noise every time I mentioned the wedding. It turned into the joke of the trip with our family and friends. They all started calling me ‘Chewy’ for short. It was silly, but now it’s a special memory of that time in our lives. Anyway, we were sailing around the coast with wedding location scouting on the brain—but we didn’t fall in love with anything until we arrived at Positano. Lo and behold, there was a 6-year-old’s birthday party taking place, and there was a 7-foot-tall Chewbacca character right in front of us making the noise. If the beauty and allure of Positano weren’t enough, this was a sign!”

Then the fun began. A friend put Whitney in touch with wedding stylist extraordinaire Cynthia Cook Smith. “From the moment I saw Cynthia’s work and spoke with her on the phone, I just adored her and her taste,” says Whitney. “She was instrumental—she helped me kick off the direction of not just the looks I would wear but the wedding itself, all the way up to the end. She suggested that the amazing Diana Sorensen of Sugokuii Events do the actual wedding, which was crucial. It’s important to have an event designer and planning team who speak the language and know all of the vendors and processes like the back of their hand.”

After the couple confirmed their event designer, Whitney and Michael did what many might call crazy and proceeded to plan an entire wedding at a venue neither of them had ever been to before. “We wanted the weekend to be as much of a surprise to us as to our guests,” Whitney explains. “I trusted our incredible planner to bring our vision to life at a place I had never been, and she and her team did an exceptional job.”

Their venue—Villa Tre Ville—came highly recommended by friends. “We could not have been more in love with it, and are so happy that’s how it worked out,” says Whitney. The aesthetic was clear from the beginning: They wanted the entire wedding to be a fun, nonstop party and a true celebration of southern Italy. They used as many local artisans as possible and wanted each evening to have a different feel, starting with the first night, which was meant to convey Capri with lemons, bougainvillea, vintage cars, and dinner in a field of lemon trees, followed by dancing at Anema e Core.

The extensive itinerary gave Cynthia and Whitney the opportunity to showcase an all-star lineup of looks. This kicked off on Thursday night with the bride wearing a couture Giambattista Valli dress with a long chiffon train that blew in the wind through the streets of Capri. During the day on Friday, Whitney soaked up the sun on the beach in an Eres maillot. And later that night, she changed into a blue silk faille strapless sweetheart gown by Oscar de la Renta. “My mom thought the handkerchief print of the swirl embroidery so perfectly evoked my now home state of Texas and was the ideal combination of Italian glamour and southern comfort,” says Whitney.

That evening centered around the luminarie—also known as festival lighting, which is famously performed in this part of Italy for special celebrations. Everyone traveled by small Italian boats from the port of the villa to the beach club around the cliff, while musicians on the water played Italian classics for the boats as they passed by. Since Whitney’s wedding dress was a classic fitted sheath, this night allowed her a glamorous Old Hollywood moment, à la Grace Kelly. Later, she changed into a short Saint Laurent sequined dress and flat Dolce & Gabbana shoes for late-night dancing.

On the morning of the big day, the bride got ready in a rose silk Cinque robe before changing into her actual wedding dress: a couture Oscar de la Renta gown made of corded rose lace with a four-foot-long train and scalloped trim. “The perfect detail to accentuate the romantic Italian setting,” notes Whitney. A cathedral-length veil billowed behind the bride as she walked down the aisle in Gianvito Rossi heels.

Michael kept things streamlined, wearing Hadleigh’s suits all weekend. For the actual wedding day, he had the Italian menswear line Isaia make tuxedos for himself and all of the groomsmen. “We loved the idea of the boys all wearing a local brand,” says Whitney. “The actual Isaia team flew all the way to Texas from Italy to fit the boys before Michael took them on a bachelor party trip, and then Mr. Isaia came over from Capri to the villa to do final fittings before the wedding!”

As the ceremony start time drew nearer, Whitney tried to stay as calm as possible despite the less than ideal weather. Positano hadn’t seen more than a light rain shower in more than five months. “The land was bone dry when we arrived a few days before the wedding . . . to the point of having a massive wildfire erupt on the hill above our rehearsal party,” explains Whitney. “But the morning of our wedding, there wasn’t just rain, there was a flash flood. Our villa had a full waterfall running down the stairs!” The forecast predicted rain until 9:00 p.m., and the wedding was tentatively canceled, as there was nowhere else in the villa to accommodate that many people at once.

“In Italy, they say rain on your wedding day is symbolic of fresh beginnings, cleansing, a pure marriage, and also a wet knot that can’t be untied,” says Whitney. “So we tried to keep that in mind and ended up drinking white wine and merging the groomsmen and bridesmaids into two connected suites at the villa and dancing in the rain until about 3:00 p.m. At that point, one of my bridesmaids, who is a meteorologist in Los Angeles, came running in saying it was going to clear that evening. We made an executive decision to pull everything together at the last minute.”

There was just one problem—the ceremony was supposed to take place on a grassy cliff, which was now soaking wet. Whitney and Michael, along with all of the bridesmaids and groomsmen, went down with dozens of towels and dried the land and the benches so that the space was ready to go. Suddenly, the sun came shining through while it was still daylight, so the wedding party was able to finish hair and makeup and get some photos taken just in time. Guests were seated at 7:30 p.m., and the ceremony began promptly at 7:45.

“We had the most majestic, special ceremony ever, and there was not a dry eye on that cliff!” says Whitney. “We never visualized ourselves standing beneath your usual floral arch. We wanted to showcase the natural beauty of the location. We wanted something organic to the area, so the florist created a flower field that was planted into the ground, and we added custom-made curved white benches for guests to sit on so everyone could see us no matter where they sat, while taking in the most incredible sea and village view of Positano.”

For dinner, Whitney changed into a custom Delphine Manivet satin slip dress and pale pink velvet Manolo Blahnik mules. Beef carpaccio with burrata, a tomato sauce ravioli, and grilled pezzogna with lemon and local vegetables were served at tables that had been custom made by local blacksmiths and decorated with colorful tiles, allowing for them to be left sans tablecloths. “We loved them so much that the tiles were shipped to us afterward, and we plan to use them in our future kids’ bathrooms,” says Whitney.

After the meal, the wedding cake was created from scratch on location. It was a typical millefoglie, served with mini fragoline and chantilly cream, but rather than being wheeled out from the kitchen, it was made on the terrace by two pastry chefs so that guests could observe the entire process. Meanwhile, Whitney slipped into a fringed, beaded Naeem Khan dress for dancing.

Everyone then retired downstairs to the Salone Bianca, which had an outside area with an Italian disco-era feel. Inside the main salone, there was boudoir-tinted lighting, tons of candles, and lanterns that emphasized the Syrian-Moroccan decor. “We really wanted to respect the different environments inside and outside, while still giving it a glamorous feel without anything too overdone or unnatural to the villa,” says Whitney. “We danced until 5:00 a.m. at least and served big bowls of pasta and mini caprese burgers with frozen Limoncello shots nonstop—All. Night. Long.”